2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin | 36475-14-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: 2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
• 英文别名: [(2S)-2,3-di(octanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 36475-14-6
• 化学式: C₂₄H₄₈NO₈P
• 分子量: 509.621
• InChiKey: YHIXRNNWDBPKPW-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [(2R)-3-[(4-methoxyphenyl)methoxy]-2-octanoyloxypropyl] octanoate 在 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 2,3-Dioctanoyl-sn-glycero-1-phosphorylcholin
  参考文献：
  名称：

  Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

  摘要：

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

  DOI：

  10.1021/jacs.5b05832

文献信息

• Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism
  作者：Tohru Taniguchi、Daisuke Manai、Masataka Shibata、Yutaka Itabashi、Kenji Monde

  DOI：10.1021/jacs.5b05832

  日期：2015.9.30

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.